ROBERTA. BENKESER AND ROLAND G. SEVERSON
1.124
[CONTRIBUTION FROM THE CHEMICAL
Vol. 73
LABORATORIES OF PURDUE UNIVERSITY ]
The Preparation and Reactions of Triphenylsilylpotassium BY ROBERTA. BENKESER AND ROLAND G. SEVERSON' Triphenylsilylpotassiurn has been prepared by the cleavage of phenylisopropyltriphenylsilanewith a sodium-potassium alloy (1:5 ) in ethyl ether. This compound couples with trirnethylchlorosilane, triethylchlorosilane and bromobenzene to form l,l,l-triphenyl-2,2,2-trirnethyldisilane,l,l,l-tripheny1-2,2,2-triethyldisilane arid tetraphenylsilane, respectively. I t reacts with hydrogen chloride to form triphenylsilane, and can be carbonated to form an unstable substance thought to be tripheuylsilanecarboxylic acid This latter material loses carbon monoxide readily to form triphenylsilanol. Further studies i n this field are nom i r i progrcsi
Introduction.-In 1933 Kraus and Eatough2 reported the preparation of triphenylsilyllithium and triphenylsilylsodium. One year later triethylsilyllithium was made by Kraus and N e l ~ o n . ~ These classical experiments represent the only successful preparation of organometallics of silicon compounds. Of necessity these workers were restricted to small scale reactions since their procedure required the use of a high vacuum system along with starting materials that in some cases were expensive and difficult to make. Both from the standpoint of chemical theory, and because of their potential usefulness in the synthesis of new types of compounds, these silicon organometallics are of considerable importance. Several workers* have reported unsuccessful attempts to prepare these reactive silicon intermediates by methods which normally produce organometallics with carbon compounds. At this time we are reporting the preparation of triphenylsilylpotassium5 by the cleavage of phenylisopropyltriphenylsilane with sodium-potassium alloy in ethyl ether6:
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(1) .4 portion of this paper is abstracted from the doctoral dissertation of Roland G Severson, Purdue University, 1931 ( 2 j C. A . Kraus and H. Eatough, THISJ O I I K N A L , 55, 3008 (1933) f R ) C. -4.Krdns and IV. K . hTeIsou.ibid.. 66, 1!13 (1!13&). ( 4 ) (a) C. E a b o r n J . Cheiir. .Yv
